Acetic Acid → 5-(4-Chlorophenyl)-2-(1-methylpiperidin-4-yl)pyrimidine

HRID 393742노트

반응식

HRID 393742 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH:19]=3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.CO.C(O)(=O)C>C(OCC)(=O)C.[Pt](=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([CH:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 887MethanolHCID 226466955-(4-Chlorophenyl)-2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine

생성물 1

HCID 226466965-(4-Chlorophenyl)-2-(1-methylpiperidin-4-yl)pyrimidine수율 45%

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 8857Ethyl Acetate용매

실험 절차

Platinum(IV) oxide (30 mg) was added to a solution of 5-(4-chlorophenyl)-2-(1-methyl-1,2,3,6-tetrahydropyridin -4-yl)pyrimidine (0.31 g) in a mixture of ethyl acetate (20 ml), methanol (3 ml) and acetic acid (1 ml) and the mixture was hydrogenated at atmospheric pressure for 18 h. The mixture was then filtered through celite, washing with 10% methanol/ethyl acetate, and evaporated under reduced pressure. The residue was treated with 2 M sodium hydroxide (15 ml) and extracted with diethyl ether (2×25 ml), and the organic extracts were washed with water (2×10 ml), saturated brine (20 ml), dried (Na2SO4) and evaporated under reduced pressure and the residue purified by silica gel column chromatography with 10% methanol/dichloromethane with 0.5% concentrated aqueous ammonia as eluent, to yield the title compound as a white solid (0.14 g, 45%).

후처리

  1. filtrationThe mixture was then filtered through celite
  2. washwashing with 10% methanol/ethyl acetate
  3. customevaporated under reduced pressure
  4. additionThe residue was treated with 2 M sodium hydroxide (15 ml)
  5. extractionextracted with diethyl ether (2×25 ml)
  6. washthe organic extracts were washed with water (2×10 ml), saturated brine (20 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customthe residue purified by silica gel column chromatography with 10% methanol/dichloromethane with 0.5% concentrated aqueous ammonia as eluent

출처 및 근거

ORD 기록
ord-ceb51a803c5445b7ae77ac2c5c6d8e76
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809100B2

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